Simple Distillation

Objectives:
1. Define the boiling point of a pure liquid and discuss why and how it is
influenced by atmospheric pressure.
2. Experimentally determine the boiling point of a pure liquid by the method of
distillation.

Background:
Liquid molecules are held together by attractive forces. A liquid in an open
container slowly evaporates because some of the molecules have enough energy to
break these attractive forces and leave the surface. Most of them migrate so far from
the surface that they never return. A liquid placed in an empty closed container will
evaporate for awhile, but eventually some of the “lost” molecules do return to the
surface to condense and rejoin the liquid itself. After a period of time, the evaporation
and condensation will be occurring at the same rate and the liquid level will no longer
change. The pressure exerted by the molecules in the gas phase is called the “vapor
pressure” of the liquid, and increasing the temperature will cause an increase in the
vapor pressure (a greater number of molecules have enough energy to break the
attractive forces). The presence of other different molecules in the space above the
liquid has no effect on vapor pressure (as long as they don’t condense), and therefore a
given liquid at a given temperature will have a given vapor pressure. Liquids with high
vapor pressures at room temperature are called “volatile” and those with low vapor
pressures at room temperature are called “nonvolatile”. Examples of vapor pressures at
25 °C are: water = 23.8 torr, methyl alcohol = 122 torr, and diethyl ether = 470 torr.

Boiling is different from evaporation. In boiling, molecules throughout the liquid

(not just those near the surface) are breaking the attractive forces. Bubbles of vapor
form anywhere within the liquid and rise to the surface. For boiling to occur, the liquid
has to be hot enough so that its vapor pressure equals the atmospheric pressure (760
torr at sea level on an average day). If the liquid is not hot enough, the bubble of vapor
will not have enough pressure to form and rise to the surface. As you can tell by the
room-temperature vapor pressures in the paragraph above, ether does not have to be
heated very much to increase its vapor pressure to 760 torr. Therefore, it has a low
boiling point (35 °C). Water, on the other hand, needs to be heated to 100 °C to boil at
normal atmospheric pressure. Also note that if the atmospheric pressure changes, the
boiling point of a substance changes. Thus, if you are in the mountains, the
atmospheric pressure is lower, and so is water’s boiling point. A pressure cooker
increases the “atmospheric pressure” inside it and the boiling water will be hotter than
100 °C. Phoenix is slightly above sea level, and boiling points determined here can be
1-2 degrees below the literature value.

Boiling points can be determined by the process of simple distillation (boiling

followed by condensation of the pure vapors, leaving solid impurities behind). If a pure
liquid is used, the temperature of the rising vapor will remain at the boiling point until it
reaches the water-cooled condenser. A pure liquid’s boiling point (corrected to sea

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level) is a good indicator of its identity. However, it is not a good indicator of its purity if
the impurities are other liquids or gases. Mixtures of liquids may have boiling points
above, below or the same as an individual component. Some, but not all, liquid
mixtures may be separated by a process of fractional distillation (next lab).

You will receive a pure liquid as an unknown, and you are to distill it and carefully
record its boiling point. Then you will identify it by comparing boiling points with the list
below. Your unknown is one of the following:

Liquid Boiling point in °C at 760 torr

pentane 36.1
dichloromethane 40.0
1-chloropropane 46.6
acetone 56.5
hexane 68.7
1-chlorobutane 78.4
cyclohexene 83.0
2-iodopropane 89.5
water 100

Procedure:
Obtain an unknown and record its number. Assume your unknown is
moderately flammable and toxic. Do not breathe the vapors unnecessarily. Use
heating mantles and controllers. Do not light Bunsen burners!
Important: Preheat the mantle at a setting of 60 volts for 10 minutes before
placing the round bottom flask in it. Place the heating mantle under the flask and adjust
the apparatus until the flask rests in the mantle. (Flask must be touching the bottom of
the mantle.)
Unscrew the round-bottom flask and add a couple of boiling stones and all of
your liquid unknown (use a funnel). Wipe any unknown off the neck of the flask and
reconnect it. Attach the apparatus to the ring stand at the still head with a micro clamp.
Connect the hoses on the condenser so that water enters the lower connection and
leaves from the upper connection and adjust the water to a very slow steady flow rate.
Be sure that the end of the water hose is directed towards the bottom of the cup sink.
(If you don’t, we may have a flood!) Check the thermometer position and all
connections, and place a small beaker under the condenser to collect the liquid. See
the diagram and picture for details of the setup. Your instructor must check your
setup before you begin!
Note: Do not “shake down” the thermometer. If you are not sure how to read
the thermometer, ask your instructor. (divisions may be I or 2 °C).
Carefully control the heat and distill the liquid. Record the temperature when the
first drop is collected (may be low due to dissolved gases), and at five-drop intervals.
Do not heat the flask to dryness. When you are finished, turn off the controller and
allow the apparatus to cool before attempting to clean it. Plot the data on the graph
provided in the lab report. The temperature range over which most of the liquid distills

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(the distillation temperature) is considered by organic chemists to be the boiling point.
Boiling points, like melting points, are always reported as ranges.

Waste Handling: Any unused portion of your unknown should be emptied in the waste
container in the hood before returning the empty vial to the supply cart. When finished
with the distillation, dispose of the unknown in the waste container in the hood.

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Report: Simple distillation Name: __________________________
Section #: ______________
Unknown # ____________
Volume, drops Temp. °C Volume, drops Temp. °C
1 45
5 50
10 55
15 60
20 65
25 70
30 75
35 80
40 85

Graph your results, and mark on the graph the beginning and the end of the boiling
point range of your unknown (ignore the 1st drop).

Experimental boiling point range ___________

Identification of unknown __________________________. If there is more than one

possibility, explain.

Questions:

1. Why are boiling chips added to the liquid before heating is begun?

2. Why is the boiling point of a compound not as useful to an organic chemist as

the melting point of a compound?

3. If a vacuum pump is hooked up to the arm of a stoppered filter flask containing

a little water, the water will boil at room temperature. Explain.

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